Solved: A student was given the structural formulas of

What is the major product obtained from the reaction of each of the following compounds with excess HCl?

Draw a structure for each of the following: a. 2-hexyne b. 5-ethyl-3-octyne c. methylacetylene d. vinylacetylene e. methoxyethyne f. sec -butyl- tert -butylacetylene g. 1-bromo-1-pentyne h. 5-methyl- 2-cyclohexenol i. diethylacetylene j. di- tert -butylacetylene k. cyclopentylacetylene l. 5,6-dimethyl-2- heptyne

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did she name correctly? Correct those that are misnamed. a. 4-ethyl-2- pentyne b. 1-bromo-4-heptyne c. 2-methyl-3-hexyne d. 3-pentyne

Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bondmaking and bond-breaking processes.

What is each compounds systematic name?

What reagents could be used to carry out the following syntheses?

Draw the structures and give the common and systematic names for alkynes with molecular formula C 7 H 12 . (Hint: There are 14.)

Explain why the following reaction results in the product shown:

How could the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?

What reagents would you use for the following syntheses? a. (Z)-3-hexene from 3-hexyne b. (E)-3-hexene from 3-hexyne c. hexane from 3-hexyne

What will be the major product of the reaction of 1 mol of propyne with each of the following reagents?

What is each compounds systematic name?

What is the molecular formula of a hydrocarbon that has 1 triple bond, 2 double bonds, 1 ring, and 32 carbons?

Answer Problem 37, parts a h using 2-butyne as the starting material instead of propyne.

What are the products of the following reactions?

a. Starting with 3-methyl-1-butyne, how could you prepare the following alcohols? 1. 2-methyl-2-butanol 2. 3-methyl-1-butanol b. In each case, a second alcohol would also be obtained. What alcohol would it be?

How many of the following names are correct? Correct those that are wrong. a. 4-heptyne c. 4-chloro- 2-pentyne e. 4,4-dimethyl-2-pentyne b. 2-ethyl-3-hexyne d. 2,3-dimethyl-5-octyne f. 2,5-dimethyl-3- hexyne

Which of the following pairs are keto-enol tautomers?

How can the following compounds be prepared using ethyne as the starting material?

Do the equilibria of the following acidbase reactions lie to the right or the left? (The p Ka of H 2 O 2 is 11.6.)

What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences?

Draw the keto tautomer for each of the following

Show how each of the following compounds could be prepared using the given starting material, any necessary inorganic reagents, and any necessary organic compound that has no more than four carbons:

A chemist was planning to synthesize 3-octyne by adding 1-bromobutane to the product obtained from the reaction of 1-butyne with sodium amide. Unfortunately, however, he had forgotten to order 1- butyne. How else can he prepare 3-octyne?

a. Explain why a single pure product is obtained from hydroborationoxidation of 2-butyne, whereas two products are obtained from hydroborationoxidation of 2-pentyne. b. Name two other internal alkynes that will yield only one product upon hydroborationoxidation.

What stereoisomers are obtained from the following reactions?

a-Farnesene is a dodecatetraene found in the waxy coating of apple skins. What is its systematic name? Include E and Z where necessary to indicate the coni guration of the double bonds.

Show how the following compounds could be synthesized starting with ethyne:

Explain why, in hydroborationoxidation, HO and HOOH cannot be added until after the hydroboration reaction is over.

Starting with ethyne, describe how the following compounds could be synthesized: a. (2 S ,3 R )- 4- bromo-3-hexanol and (2 R ,3 S )- 4-bromo-3-hexanol b. (2 R ,3 R )- 4-bromo-3-hexanol and (2 S ,3 S )- 4-bromo-3-hexanol

What are the products of the following reactions?

Problem 1P What is the molecular formula for a cyclic hydrocarbon with 14 carbons and two triple bonds?

Problem 2P Draw the structure for each of the following: a. 1-chloro-3-hexyne d. sec-butylisobutylacetylene b. cyclooctyne e. 4,4-dimethyl-1-pentyne c. isopropylacetylene f. dimethylacetylene

Problem 3P Draw the structures and give the common and systematic names for the seven alkynes with molecular formula C6H10.

Problem 14P What ketones would be formed from the acid-catalyzed addition of water to 3-heptyne?

Which alkyne would be the best one to use for the synthesis of each of the following ketones?

Draw all the enol tautomers for each of the ketones in Problem \(15\). Equation Transcription: Text Transcription: 15

Problem 27P Give the major product obtained from the reaction of each of the following with excess HCI: a. CH3CH2C?CH b. CH3CH2C?CCH2CH3 c. CH3CH2C?CCH2CH2CH3

Problem 28P Draw a structure for each of the following: a. 2-hexyne b. 5-ethyl-3-octyne c. methylacetylene d. vinylacetylene e. methoxyethyne f. sec-butyl-tert-butylacetylene g. 1-bromo-1-pentyne h. 5-methyl-2-cyclohexenol i. diethylacetylene j. di-tert-butylacetylene k. cyclopentylacetylene l. 5,6-dimethyl-2-heptyne

Problem 29P A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did she name correctly? Correct those that are misnamed. a. 4-ethyl-2-pentyne b. 1-bromo-4-heptyne c. 2-methyl-3-hexyne d. 3-pentyne

Problem 39P What is the molecular formula of a hydrocarbon that has 1 triple bond, 2 double bonds, 1 ring, and 32 carbons?

Problem 40P Answer Problem 37, parts a–h using 2-butyne as the starting material instead of propyne. What will be the major product of the reaction of 1 mol of propyne with each of the following reagents? a. HBr (1 mol) b. HBr (2 mol) c. Br2 (1 mol)/CH2Cl2 d. Br2 (2 mol)/CH2Cl2 e. aqueous H2SO4, HgSO4 f. R2BH in THF followed by H2O2/HO-/H2O g. excess H2, Pd/C h. H2/Lindlar catalyst i. sodium amide j. the product of part i followed by 1-chloropropane

What are the products of the following reactions?

Problem 51P a. Explain why a single pure product is obtained from hydroboration–oxidation of 2-butyne, whereas two products are obtained from hydroboration–oxidation of 2-pentyne. b. Name two other internal alkynes that will yield only one product upon hydroboration–oxidation.

What stereoisomers are obtained from the following reactions?

\(\alpha\)-Farnesene is a dodecatetraene found in the waxy coating of apple skins. What is its systematic name? Include \(E \text { and } Z\) where necessary to indicate the configuration of the double bonds. Equation Transcription: Text Transcription: alpha E and Z

Name the following:

Name the following:

Problem 43P How many of the following names are correct? Correct the incorrect names. a. 4-heptyne b. 2-ethyl-3-hexyne c. 4-chloro-2-pentyne d. 2,3-dimethyl-5-octyne e. 4,4-dimethyl-2-pentyne f. 2,5-dimethyl-3-hexyne

Problem 55P Explain why, in hydroboration–oxidation, HO– and HOOH cannot be added until after the hydroboration reaction is over.

Name the following:

Problem 17P For each of the following alkynes, draw the products of (1) the acid-catalyzed addition of water (mercuric ion is added for part a) and (2) hydroboration–oxidation: a. 1-butyne b. 2-butyne c. 2-pentyne

There is only one alkyne that forms an aldehyde when it undergoes the mercuric-ion-catalyzed addition of water. Identify the alkyne.

Problem 19P Describe the alkyne you would start with and the reagents you would use if you wanted to Synthesize a. Pentane. b. Cis-2-butene. c. trans-2-pentene. d. 1-hexene.

Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.

Problem 31P What is each compound’s systematic name?

What reagents could be used to carry out the following syntheses?

Problem 42P a. Starting with 3-methyl-1-butyne, how could you prepare the following alcohols? 1. 2-methyl-2-butanol 2. 3-methyl-1-butanol b. In each case, a second alcohol would also be obtained. What alcohol would it be?

Which of the following pairs are \(\text { keto-enol }\) tautomers? Equation Transcription: Text Transcription: keto-enol

Problem 54P Show how the following compounds could be synthesized starting with ethyne: a. Cis-2-octene b. trans-3-heptene

Problem 56P Starting with ethyne, describe how the following compounds could be synthesized: a. (3S,4R)- 4-bromo-3-hexanol and (3R,4S)- 4-bromo-3-hexanol b. (3R,4R)- 4-bromo-3-hexanol and (3S,4S)- 4-bromo-3-hexanol

Problem 33P Draw the structures and give the common and systematic names for alkynes with molecular formula C7H12. (Hint: There are 14.)

Explain why the following reaction results in the product shown:

How could the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?

How can the following compounds be prepared using ethyne as the starting material?

Do the equilibria of the following acid–base reactions lie to the right or the left? (The \(p K_{a}\) of \(\mathrm{H}_{2} \mathrm{O}_{2}\) is \(11.6\).) \(\mathrm{HOOH}+\mathrm{HO}^{-} \rightleftharpoons \mathrm{HOO}^{-}+\mathrm{H}_{2} \mathrm{O}\) \(R C \equiv \mathrm{CH}+\mathrm{HOO}^{-} \rightleftharpoons R \mathrm{C} \equiv \mathrm{C}^{-}+\mathrm{HOOH}\) Equation Transcription: ? ??? Text Transcription: pK_a H_2 O_2 11.6 HOOH + HO^- right left harpoons HOO^- + H_2 O RC trigram CH + HOO^- right left harpoons RC trigram C^- + HOOH

Problem 47P What stereoisomers are obtained when 2-butyne undergoes each of the following reaction sequences? a. 1. H2/Lindlar catalyst 2. Br2/CH2Cl2 b. 1. Na/NH3(liq), –78 oC 2. Br2/CH2Cl2 c. 1. Cl2/CH2Cl2 2. Br2/CH2Cl2

Problem 57P What are the products of the following reactions?

How could the following compounds be synthesized from acetylene? a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}\) Equation Transcription: ? ? Text Transcription: CH_3 CH_2 CH_2 C trigram CH CH_3 CH trigram CH_2

Problem 36P What reagents would you use for the following syntheses? a. (Z)-3-hexene from 3-hexyne b. (E)-3-hexene from 3-hexyne c. hexane from 3-hexyne

Problem 37P What will be the major product of the reaction of 1 mol of propyne with each of the following reagents? a. HBr (1 mol) b. HBr (2 mol) c. Br2 (1 mol)/CH2Cl2 d. Br2 (2 mol)/CH2Cl2 e. aqueous H2SO4, HgSO4 f. R2BH in THF followed by H2O2/HO-/H2O g. excess H2, Pd/C h. H2/Lindlar catalyst i. sodium amide j. the product of part i followed by 1-chloropropane

What is each compound’s systematic name? a. \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH} \equiv \mathrm{CH}_{2}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH}\) Equation Transcription: ?? ?? Text Transcription: CH_3 C trigram CCH_2 CH_2 CH_2 CH trigram CH_2 CH_3 CH_2 C trigram CCH_2 CH_2 C trigram CH

Draw the keto tautomer for each of the following:

Show how each of the following compounds could be prepared using the given starting material, any necessary inorganic reagents, and any necessary organic compound that has no more than four carbons:

Problem 50P A chemist was planning to synthesize 3-octyne by adding 1-bromobutane to the product obtained from the reaction of 1-butyne with sodium amide. Unfortunately, however, he had forgotten to order 1-butyne. How else can he prepare 3-octyne?

Name the following:

In Table \(7.2\) , what is the smallest alkane, the smallest terminal alkene, and the smallest terminal alkyne that are liquids at room temperature, which is generally taken to be \(20^{\circ} \mathrm{C} \text { to } 25^{\circ} \mathrm{C}\)? Equation Transcription: ° to ° Text Transcription: 7.2 20 degrees C to 25 degrees C

Problem 9P Why does cis-2-butene have a higher boiling point than trans-2-butene?

What are products of the following reactions?

Problem 21P Explain why sodium amide cannot be used to form a carbanion from an alkane in a reaction that favors products.

Problem 22P Any base whose conjugate acid has a pKa greater than ______ can remove a proton from a terminal alkyne to form an acetylide ion (in a reaction that favors products).

What orbitals are used to form the carbon–carbon ? bond between the highlighted carbons? 1. \(\mathrm{CH}_{3} \mathrm{CHCHCH}_{2}\) d. \(\mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CCH}_{3}\) g. \(\mathrm{CH} 3 \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH} 3\) 2. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) e. \(\mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{CCH}_{3}\) h. \(\mathrm{CH} 3 \mathrm{C} \equiv \mathrm{CCH}_{2} \mathrm{CH} 3\) 3. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}=\mathrm{CH}_{2}\) f. \(\mathrm{CH}_{2}=\mathrm{CHCH}=\mathrm{CH}_{2}\) i. \(\mathrm{CH}_{2}=\mathrm{CHC} \equiv \mathrm{CH}\) Equation Transcription: ? ? ? ? Text Transcription: CH_3 CH CHCH_2 CH_3 CH=CHCH_3 CH_3 CH=C=CH_2 CH_2 C trigram CCH_3 CH_3 C trigram CCH_3 CH3CH=CHCH_2 CH3 CH3C trigram CCH_2 CH3 CH_2 =CHC trigram CH

What is the major product of each of the following reactions?

Problem 13P Drawing on what you know about the stereochemistry of alkene addition reactions: a. write the mechanism for the reaction of 2-butyne with one equivalent of Br2. b. predict the configuration of the product of the reaction.

List the following in order from strongest base to weakest base: a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\overline{\mathrm{C}} \mathrm{H} \quad \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{C}^{-} \quad \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \overline{\mathrm{C}} \mathrm{H}_{2}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-} \quad \mathrm{F}^{-} \quad \mathrm{CH}_{3} \mathrm{C} \equiv \mathrm{C}^{-} \quad{ }^{-} \mathrm{NH}_{2}\) Equation Transcription: ? ? Text Transcription: CH_3 CH_2 CH=overlineC H CH_3 CH_2 C trigram overlineC CH_3 CH_2 CH_2 overlineCH_2 CH_3 CH_2 O^- F^- CH_3 C trigram C^- ^-NH_2

Which carbocation is more stable? a. \(\mathrm{CH}_{3} \mathrm{C}^{+} \mathrm{H}_{2} \text { or } \mathrm{H}_{2} \mathrm{C}=\mathrm{C}^{+} \mathrm{H}\) b. \(H_{2} C=C^{+} H \text { or } H C \equiv C^{+}\) Equation Transcription: ? Text Transcription: CH_3 C^+ H_2 or H_2 C=C^+ H H_2 C=C^+H or HC trigram C^+